Neighbouring Group Participation - NGP By A Cyclopropane, Cyclobutane or A Homoallyl Group

NGP By A Cyclopropane, Cyclobutane or A Homoallyl Group

If Cyclopropylmethyl chloride is reacted with ethanol and water then a mixture of 48% cyclopropylmethyl alcohol, 47% cyclobutanol and 5% homoallyl alcohol (but-3-enol) is obtained. This is because the carbocationic intermidate is delocalised onto many different carbons through a reversible ring opening.

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